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Quiksilver07070
Quiksilver07070, Computer Support Specialist
Category: Software
Satisfied Customers: 793
Experience:  Install, Update, troubleshoot and remove all types of software
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I need your help - with Outlook 2016 & icloud sync I have a

Customer Question

I need your help - with Outlook 2016 & icloud syncI have a dell pc with Windows 10 pro installed. I am trying to use iCloud control panel that allows the PC to utilize your contacts calendars etc with iCloud via outlook 2016.However it doesn't operate. When I click the Check box for use contacts calendars via the icloud control panel either doesn't stay checked or with say "setting up" for hours. With no luck either way.I do know that outlook 2016 will work with Windows 10 as my other computer which is win 10 and outlook 2016 works fine.thank you for your help!
Submitted: 9 months ago.
Category: Software
Expert:  Quiksilver07070 replied 9 months ago.

Hello and thank you for choosing JustAnswer.com

.

My name is ***** ***** will be the expert helping you. Just so you know, I am reviewing your question, and need a few minutes to digest and respond back to you.

Please Stand By

Customer: replied 9 months ago.
ok
Expert:  Quiksilver07070 replied 9 months ago.

This can be a difficult thing to pin down and figure out.

We wont aim on the WHY so much, as we will concentrate on the FIX......if possible.

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Something to keep in mind about this issue.....Outlook is a MICROSOFT application, and iCloud is an APPLE application.

Now we all know Apple and Microsoft are competitors, and only work together if there is MASS amounts of money to be made. Hence iCloud for Windows, and Outlook for mac (as examples)

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We may come to the conclusion, that there is a bug that has YET to be vetted out, and will render this issue NOT FIXABLE.

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With that said, I will do my absolute best, ***** ***** not give up, until I have bonafide proof, that sides on fixable or not.

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So......lets do some initial troubleshooting first.

Turn iCloud Calendar, Contacts and Reminders off and back on

  1. Close Outlook.
  2. Open iCloud for Windows.
  3. Deselect the Mail, Contacts, Calendars & Tasks checkbox and click Apply.
  4. Wait a few seconds. Select Mail, Contacts, Calendars & Tasks, and click Apply.
  5. Open Outlook.
Customer: replied 9 months ago.
I have unistalled; installed and it does not work - it was working about a week ago an now its not
Expert:  Quiksilver07070 replied 9 months ago.

Okay, uninstalling and REinstalling is a good troubleshooting step.

But have you done the instructions ABOVE SPECIFICALLY?

Customer: replied 9 months ago.
I havesometimes the box will not stay checked; if it does try to "install" it will say setting up & can stay that way for hourshave you had experience with this issue ?
Expert:  Quiksilver07070 replied 9 months ago.

Please keep in mind that troubleshooting a problem piece of software can take some time......and an instant solution is rarely the fix.

I ask that we both be patient, and we will get to the bottom of the issue.

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I have used Outlook 2016, and i have used icloud for windows.......i chose NOT to use them TOGETHER, because they are made by competitive companies......a different MORE FRIENDLY application is best suited instead of using iCloud. Google Drive comes to mind, and thats just one that works on Apple and Windows machines.

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Experience with THIS SPECIFIC issue....NO......but i dont think this particular issue is common, and not many experts WOULD have experience with this issue.

Can i replicate the issue.....not yet.....from my end, the icould and outlook 2016 is working on my computer.

But we dont have the SAME hardware.......thats why i asked what the MAKE and MODEL is of the computer you are using.

Expert:  Quiksilver07070 replied 9 months ago.

correction....that is why i am asking what is the MAKE and MODEL of your computer?

I know you mentioned DELL......do you have a service tag number?

Customer: replied 9 months ago.
dell win 10 inspirion 3847
Expert:  Quiksilver07070 replied 9 months ago.

thank you.

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Are all your Windows 10 updates installed? (which shoudl include any updates for MS OFFice and OUtlook2016)

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When you UNinstalled icloud, and then REinstalled it.....did you DOWNLOAD the newest version of iCloud for Windows (v5.1)?

If you dont know.....i suggest UNinstalling iCloud, then do a computer RESTART, this will hep REalign the OS again within the RAM.

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Then DOWNLOAD the newest iCloud for Windows v5.1 from here:

https://support.apple.com/en-us/HT204283

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Then install after you download.

This ensures you have the latest version with all the necessary patches and fixes applied.

Customer: replied 9 months ago.
actually control panel is up to version 5.2x
Customer: replied 9 months ago.
all updates are installed
Expert:  Quiksilver07070 replied 9 months ago.

Where are you seeing V5.2?

Website shows V5.1

Expert:  Quiksilver07070 replied 9 months ago.

Oh i see it now.

The App shows the verison in the upper R-hand corner

Showing V5.2.1

Customer: replied 9 months ago.
we have 2 computers; my computer control panel says 5.2.1
Expert:  Quiksilver07070 replied 9 months ago.

okay....WHERE are you doing the CHECK boxes that WONT stay checked?

Is it Within the OUtlook 2016 program?

or

Is it within the iCould Program?

or

is it within the icloud WEBSITE (which uses the Web browser program)

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Which is it?

Customer: replied 9 months ago.
in the control panel (icloud) you check the box for contacts etc - at first it says setting up but does not initiate after that....then checking the box only stays temp checked
Expert:  Quiksilver07070 replied 9 months ago.

Please take a screen shot......my icloud for windows does NOT have a check box for CONTACTS.

.

Instead it says to go online to look at and manage contacts and calendar.

See my screen shot:

Customer: replied 9 months ago.
pls see attached
Expert:  Quiksilver07070 replied 9 months ago.

When you put a check mark in the check box for the CONTACTS......does the APPLY button (at the bottom of the icloud control panel) become available to click?

So, in the image i see the check mark, but the APPLY is greyed out.

Which means that the check mark is ALREADY recognized.

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So, you may have to UNcheck the contacts.....then hit apply.

Then check the contacts and hit apply AGAIN.

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This is tken RIGHT from the icloud troubleshooting steps.

And we are almost at the END of the list.

Expert:  Quiksilver07070 replied 9 months ago.

The next step is to:

Make sure that the iCloud Outlook Add-in is on

The iCloud Outlook Add-in transfers your content between iCloud and Outlook. Follow these steps to turn on the Add-in:

Open Outlook 2016 and then:

  1. Select the File menu.
  2. Click Options in the left panel.
  3. Click Add-ins in the left panel of the Outlook Options window.
  4. Look at the list of add-ins in the Active Application Add-ins section.
  5. Select the iCloud Outlook Add-in.
Expert:  Quiksilver07070 replied 9 months ago.

KEEP THIS IN MIND!

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Some iCloud features in Outlook work differently than they do on your Apple device. Here are a few tips to help you use Outlook with iCloud for Windows.

Contacts

  • Outlook will only import the first contact in a vCard set.
  • If you need to add a vCard set to Outlook, import the set directly into iCloud.com or OS X Contacts. We will bundle the entire set for you and add them as individuals to the your Contacts.

Calendars

  • When you add Calendar attachments to a Calendar entry in Outlook, you won't see them in Calendar for iOS, Calendar for OS X Mountain Lion, or iCal. (or the other way around)

Reminders (Tasks)

  • Like Calendars and Contacts, you need to enter your Reminders in the iCloud section of Tasks in Outlook. If you don't enter your Tasks into the iCloud section, they won't transfer to iCloud.
Customer: replied 9 months ago.
the add on is on
Expert:  Quiksilver07070 replied 9 months ago.

Did you check the iCloud Add-On for Outlook?

What was the results?

Expert:  Quiksilver07070 replied 9 months ago.

Sorry.....okay....we are now at the LAST step, for documented troubleshooting, beyond this.......I work on instinct, and MAY need to have acccess to your computer through remote session to continue to troubleshoot.

.

Last documented step:

Make sure that iCloud isn’t your default account in Data Files.

When iCloud is set as your default account in Data Files, your data won't sync between your devices.

Open Outlook and then do the following:

  1. Select File > Info > Account Settings > Data Files.
  2. If iCloud is listed as the default account in the Comments column, select a different account.
  3. Click Set as Default.
  4. Close Outlook
  5. Restart computer.
Customer: replied 9 months ago.
the only data file - is for outlook - there is not one for icloud....I think that file is missing ?
Expert:  Quiksilver07070 replied 9 months ago.

Thats okay, thats normal.....because you DONT have an icloud email address

Customer: replied 9 months ago.
this shows from my computer - yet the bottom file is Not on my wife's computer (computer with the issue)
Customer: replied 9 months ago.
I don't have an icloud email address either
Expert:  Quiksilver07070 replied 9 months ago.

The last thing i can think of, would be to just CREATE an icloud Email address, that may purge the icloud issue.

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Its a hunch......as most people dont use icloud WITHOUT having the Email address to go with it.

YOu dont have to USE it.....but this might be whats causing the issue.

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If that fails to work.....we would need to do a remote session, so i can go through all the settings.

Customer: replied 9 months ago.
ok pls hold
Expert:  Quiksilver07070 replied 9 months ago.

Remember to RESTART the computer when instructed.

We ask folks to do things that may SEEM trivial.....but we have very VERY good reason.....and to explain them all, would take forever.

I think you understand this......but sometimes peope take it upon themself to ignore certain tasks based on fear or indecision, or know how.

The remote session takes this problem OUT OF THE EQUATION, and allows ME to SEE and control the computer directly.

Expert:  Quiksilver07070 replied 9 months ago.

Also.....for contacts to SYNC across ALL computers.....you MUST login to the iCloud control Panel Program, using the SAME icloud ACCOUNT and PASSWORD.

So your wifes computer, and YOUR computer both have icloud App, and you login to only a single icloud account on BOTH computers.

Just FYI

Customer: replied 9 months ago.
creating the icloud acct didn't change anything =(
Expert:  Quiksilver07070 replied 9 months ago.

Hmmmmm....

Cant help but think something was missed, or overlooked.

Expert:  Quiksilver07070 replied 9 months ago.

What Program do yo use to VIEW the contacts? Outlook?

Customer: replied 9 months ago.
Expert:  Quiksilver07070 replied 9 months ago.

okay......and how can you tell its not working?

Expert:  Quiksilver07070 replied 9 months ago.

Have you tried to ADD a contact and see if it syncs across the 2 computers with icloud for windows and OUTLOOK?

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Both computers need to have icoud for windows, and both computers need to have outlook with the Add-on for icloud turned on.

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Also you need to logged in to the icloud for windows APP using the SAME account on BOTH computers.

Expert:  Quiksilver07070 replied 9 months ago.

I have found some disheartening information across the web, from Microsft Forums to Apple Forums.

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The issue here AGAIN, is that icloud is made by APPLE, and outlook is made by MICROSOFT. These are 2 COMPETEING companies, they rarely play well together, and in some cases, accusations of sabotage have been reported. Where by software made to be compatible......is not. And then each company POINTS the finger at each other. Neither taking the blame.....and the problem remains UNFIXED.

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YOu may have one of these issues.

Although most of these reports stem back FROM late 2015 to early 2016, a newer version of icloud which was supposed to address this issue among many others, was released (Version 5.2)

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But still there are rare useres reporting this......YOU being some of the first.

Expert:  Quiksilver07070 replied 9 months ago.

Here is the Apple forum showing the newest version 5.2 is not syncing with outlook 2016

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I am revviewing it now. YOu can too, if you like?

https://discussions.apple.com/thread/7590555?start=0&tstart=0

Customer: replied 9 months ago.
thx i will look
Expert:  Quiksilver07070 replied 9 months ago.

Okay, I think i may have found a possible WORK AROUND, and it IS RELATED to the updates for MS OFFICE outlook

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Reverting outlook 2016 BUILD VERSION back to a build that is known to work (16.0.6868.2067), we just might be able to get icoud to sync once again, like normal.

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Its a fairly indepth process, and not really advisable for novices, but if you are willing to try, I will give you the instructions.

Expert:  Quiksilver07070 replied 9 months ago.

In a nutshell the process is as follows:

Reverted the last Office update, then reinstalled iCloud and the Outlook sync should work now.

Expert:  Quiksilver07070 replied 9 months ago.

Here is the instructions (FROM MICROSOFT DIRECTLY) to revert outlook (office 2016 CTR) back to a previous build

https://support.microsoft.com/en-us/kb/2770432

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Please follow the instructions, and please let me KNOW.

Please also take a moment to RATE my performance, or leave a gratuity if you received top service.

Thank you!

Customer: replied 9 months ago.
not working - can you refer me elsewhere ?

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